117322-30-2

Basic information

• Product Name: Fmoc-cycloleucine
• Synonyms: FMoc-AC5C-OH(FMoc-1-aMinocyclopentane-1-carboxylic acid);Cyclopentanecarboxylicacid, 1-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-;Fmoc-1-aminocyclopentane-1-carboxylic acid≥ 98% (HPLC);FMOC-AC5C-OH;FMOC-1-AMINOCYCLOPENTANE-1-CARBOXYLIC ACID;FMOC-1-AMINOCYCLOPENTANECARBOXYLIC ACID;FMOC-1-AMINO-1-CYCLOPENTANECARBOXYLIC ACID;FMOC-NH(1)CPEN-OH
• CAS NO: 117322-30-2
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.4
• EINECS: 2017-001-1
• Product Categories: Piperidones ,Piperidines ,Homopiperidines;FMOC;Amino Acids
• Mol File: 117322-30-2.mol
• Article Data: 7

Chemical Properties

• Melting Point: 187 °C(dec.)
• Boiling Point: 579.444 °C at 760 mmHg
• Flash Point: 304.237 °C
• Appearance: /
• Density: 1.327 g/cm³
• Vapor Pressure: 2.87E-14mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: soluble in Dimethylformamide
• PKA: 4.08±0.20(Predicted)
• BRN: 5995036
• CAS DataBase Reference: Fmoc-cycloleucine(CAS DataBase Reference)
• NIST Chemistry Reference: Fmoc-cycloleucine(117322-30-2)
• EPA Substance Registry System: Fmoc-cycloleucine(117322-30-2)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 117322-30-2(Hazardous Substances Data)

Usage

Description

Fmoc-cycloleucine, also known as 9-fluorenylmethoxycarbonyl-cycloleucine, is a synthetic amino acid derivative characterized by the presence of a fluorenylmethyloxycarbonyl (Fmoc) protecting group. This white powder is a key component in the synthesis of peptides and proteins, particularly in the development of selective inhibitors targeting nuclear hormone receptors.

Uses

Used in Pharmaceutical Industry:
Fmoc-cycloleucine is used as a reagent for the development of selective inhibitors of nuclear hormone receptors. Its incorporation into peptide sequences allows for the creation of molecules with high specificity and affinity for these receptors, which can be crucial in the treatment of various diseases and conditions related to hormonal imbalances or receptor dysregulation.
Used in Peptide Synthesis:
In the field of peptide synthesis, Fmoc-cycloleucine is utilized as a building block for the assembly of complex peptide structures. The Fmoc protecting group ensures that the cycloleucine residue remains protected from unwanted side reactions during the synthesis process, allowing for the precise and controlled construction of the desired peptide sequence.
Used in Research and Development:
Fmoc-cycloleucine is also employed in research and development settings, where it can be used to study the structure, function, and interactions of nuclear hormone receptors. By incorporating this amino acid derivative into various peptide sequences, researchers can gain insights into the molecular mechanisms underlying receptor activation, inhibition, and signaling pathways, ultimately contributing to the advancement of therapeutic strategies and drug discovery.

InChI:InChI=1/C21H21NO4/c23-19(24)21(11-5-6-12-21)22-20(25)26-13-18-16-9-3-1-7-14(16)15-8-2-4-10-17(15)18/h1-4,7-10,18H,5-6,11-13H2,(H,22,25)(H,23,24)/p-1

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 52-52-8 1-amino-1-cyclopentanecarboxylic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 6940-78-9 4-chlorobutyl bromide 
• 497-19-8 sodium carbonate 

Downstream Products

• 1453814-92-0 C₂₉H₂₇F₆N₃O₃ 
• 1398717-89-9 (S)-1-amino-N-(1-cyano-2-(4'-((4-methylpiperazin-1-yl)methyl)biphenyl-4-yl)ethyl)cyclopentanecarboxamide 
• 1398718-52-9 (S)-(9H-fluoren-9-yl)methyl 1-(1-cyano-2-(4'-((4-methylpiperazin-1-yl)methyl)biphenyl-4-yl)ethylcarbamoyl)cyclopentylcarbamate 
• 53123-88-9 sirolimus 
• 151257-08-8 tert-butyl-4'-<(2-n-butyl-4-oxo-1,3-diazaspiro<4.4>nonan-3-yl)methyl>biphenyl-2-carboxylate 

Relevant articles and documents

Exploration of N-(2-aminoethyl)piperidine-4-carboxamide as a potential scaffold for development of VEGFR-2, ERK-2 and Abl-1 multikinase inhibitor

VEGFR, ERK and Abl had been respectively identified as good drug targets, and their crosstalk also had been well elaborated. Multitarget drugs were more advantageous for cancer treatment, however, no inhibitors simultaneously acting on the three proteins were developed due to their structural diversities. Herein, N-(4-((2-(2-(naphthaen-1-yl)acetamido)ethyl)carbamoyl)piperidin-4-yl)-6- (trifluoromethyl)nicotinamide (NEPT, 6a) was discovered as an active scaffold against VEGFR-2, ERK-2 and Abl-1 kinases through the combination of support vector machine, similarity searching and molecular docking. NEPT and its derivatives were synthesized by convenient routine, their in vitro anti-proliferative abilities against human liver cancer cell line HepG2 were preliminarily evaluated. A representative compound 6b showed an IC50 value of 11.3 μM and induced significant HepG2 cells apoptosis. Besides, these compounds displayed better anti-proliferative abilities against K562 cells (a cell line with typical hyperactivity of the above multikinases), for example compound 6b exhibited an IC50 value of 4.5 μM. Based on hepatotoxicity case reports of Abl inhibitors, cytotoxicity of synthetic compounds against normal liver cell lines (QSG7701 and HL7702) was studied, 6b had a similar toxic effect with positive control imatinib, and most compounds showed less than 35% inhibition activities at 100 μM. Molecular docking study disclosed interactions of 6b with VEGFR-2, ERK-2 and Abl-1 kinases, respectively. Our data suggested the biological activities of 6b may derived from collaborative effects of VEGFR-2, ERK-2 and Abl-1 inhibition.

Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids

Alkylation of the benzophenone imine of glycine Wang resin with α,ω-dihaloalkanes yielded valuable reactive intermediates. These racemic ω-chloro or ω-bromo intermediates were converted to α-amino acids containing diverse side-chain functionalities (e.g.

Zinc promoted rapid and efficient synthesis of Fmoc- and Z-α,α-dialkylamino acids under neutral conditions

The introduction of Nα-9-fluorenylmethyloxycarbonyl (Fmoc) and benzyloxycarbonyl (Z) groups into α,α-dialkylamino acids is described at neutral pH using Fmoc-Cl or Z-Cl as an acylating agent respectively in the presence of activated zing powder. The reaction is simple, fast and clean. It also permits the scale up with high yields. It is completely free from protected oligomer formation, which is a known side-reaction when Schotten-Baumann procedure is followed. All the Fmoc- and Z-amino acids prepared have been fully characterized.